Outlook requires VPN to access exchange, Apple Mail does not - why?
March 16, 2015 10:30 PM   Subscribe

Outlook requires VPN to access my work exchange account, while Apple Mail does not - why?

My employer has stated that access to our exchange server offsite is only available through a VPN, and true enough when I try and access it using Outlook 2016 preview for Mac, it won't connect unless through our organisational VPN. However, when I use Apple Mail to connect to the exchange server, a VPN is not required. My office's IT guy has no idea why, and neither do I.

The policy itself is rather non-sensical since we have always been able to access it using mobile devices without the VPN (i guess because of activesync?), but I'm just trying to understand what the technical explanation for this could be in the non-mobile context. It's repeatable on both my 2013 Macbook Air and my 2012 Mac Mini, both running the latest version of Yosemite. Any ideas why this could be?
posted by modernnomad to Computers & Internet (8 answers total) 1 user marked this as a favorite
 
Google brings up this site which explains that there are two different protocols to access an Exchange server. I'm guessing this is what's happening in your case.
posted by praiseb at 10:49 PM on March 16, 2015


For me, at least, it's the difference between setting it up as an exchange account vs. IMAP/POP. Is it set up as exchange account in Apple Mail and in Ourlook?
posted by mercredi at 7:20 AM on March 17, 2015


Outlook uses the Exchange protocol, which needs to be on the same network (via vpn if necessary).
Phone clients use the ActiveSync protocol, which doesn't need the VPN, as long your administrator provides the correct connectivity (which it sounds like they have.)
There is now an option called Outlook Anywhere that allows Outlook to connect to your Exchange server without VPN. It needs specifically enabling by your administrator. If they need pointing in the right direction, "Outlook Anywhere" is the magic phrase.
posted by blue_wardrobe at 9:22 AM on March 17, 2015


They have their exchange server configured weird. The mail server is listening on a public (internet-wide) address where IMAP/POP are available to mobile and mac devices, while the proprietary outlook to exchange protocol (MAPI?) is only listening on the internal network address.

There is little security reason to do this.
posted by nickggully at 6:17 PM on March 17, 2015


Response by poster: Both are configured using exchange, not IMAP. I'm not complaining, because it used to be a huge hassle to start my VPN just to check work email from the desktop (the change happened when they upgraded exchange server 2007 to a newer version, though I'm not sure which). I'd rather use Outlook than Apple Mail, but it's generally fine. I was just curious if there was some way I could get Outlook to avoid the VPN requirement as well.
posted by modernnomad at 6:57 PM on March 17, 2015


Yes - by asking the administrator to configure the Outlook Anywhere option. See here for details.
posted by blue_wardrobe at 7:37 PM on March 17, 2015


Response by poster: thanks, I will pass that along. But that doesn't explain why Outlook would require Outlook Anywhere to be activated but Apple Mail wouldn't, does it? How does Apple Mail get around the VPN requirement other exchange clients require? As far as I know, the desktop version of Apple Mail does not have activesync.
posted by modernnomad at 7:55 PM on March 17, 2015


Maybe Apple Mail is using it already. Have you checked this page?
posted by blue_wardrobe at 8:33 PM on March 17, 2015


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